Phosphoryl-acylamines for inhibiting plant growth

Abstract

Phosphorylthio-acetyl derivatives of decahydroquinolines, octahydroindoles and octahydropyrindines are effective plant regulating agents (growth regulators and selective herbicides) and fungicides.

What is claimed is: 
     
       1. A composition for inhibiting plant growth which comprises (1) as active ingredient a compound of the formula ##SPC6## wherein each of R 1  and R 2  is hydrogen or methyl; R 3  is alkyl or haloalkyl, the alkyl groups having from 1 to 4 carbon atoms; R 4  is alkyl, alkoxy, haloalkoxy, alkylthio, the alkyl groups having from 1 to 4 carbon atoms, or amino; X is oxygen or sulphur; and m is zero or 1; and (2) a suitable carrier.   
     
     
       2. A composition according to claim 1 in which the compound is of the formula ##SPC7## wherein each of R 1  and R 2  is hydrogen or methyl; R 3  is alkyl or haloalkyl, the alkyl groups having from 1 to 4 carbon atoms; R 4  is alkyl, alkoxy, haloalkoxy, alkylthio, the alkyl groups having from 1 to 4 carbon atoms, or amino; and X is oxygen or sulphur.   
     
     
       3. A composition according to claim 1 in which the compound is of the formula ##SPC8## wherein each of R 1  and R 2  is hydrogen or methyl; R 3  is alkyl of from 1 to 4 carbon atoms; R 4  is alkyl, alkoxy or alkylthio, the alkyl groups having from 1 to 4 carbon atoms; and X is oxygen or sulphur.   
     
     
       4. A method for inhibiting plant growth which comprises applying to the plants a growth inhibiting amount of a compound of the formula ##SPC9## wherein each of R 1  and R 2  is hydrogen or methyl; R 3  is alkyl or haloalkyl, the alkyl groups having from 1 to 4 carbon atoms; R 4  is alkyl, alkoxy, haloalkoxy, alkylthio, the alkyl groups having from 1 to 4 carbon atoms, or amino; m is 0 or 1; and X is oxygen or sulphur.   
     
     
       5. A method according to claim 4 in which the compound is of the formula ##SPC10## wherein each of R 1  and R 2  is hydrogen or methyl; R 3  is alkyl or haloalkyl, the alkyl groups having from 1 to 4 carbon atoms; R 4  is alkyl, alkoxy, haloalkoxy, alkylthio, the alkyl groups having from 1 to 4 carbon atoms, or amino; and X is oxygen or sulphur.   
     
     
       6. A method according to claim 5 in which R 2  is hydrogen, R 3  is alkyl of from 1 to 3 carbon atoms and R 4  is alkoxy of from 1 to 3 carbon atoms. 
     
     
       7. The method according to claim 6 in which the compound is 1-(0,0-di-n-propyl-thiophosphorylthio-acetyl)-cis-decahydroquinoline 
     
     
       8. The method according to claim 5 in which the compound is 1-(0-ethyl-S-n-propyl-thiophosphorylthio-acetyl)-cis-decahydroquinoline. 
     
     
       9. The method according to claim 6 in which the compound is 1-(0,0-di-ethyl-thiophosphorylthioacetyl)-cis-decahydroquinoline. 
     
     
       10. The method according to claim 6 in which the compound is 1-(0,0-di-ethyl-thiophosphorylthioacetyl)-transdecahydroquinoline. 
     
     
       11. The method according to claim 6 in which the compound is 1-(0,0-di-ethylthiophosphorylthioacetyl)-cis-decahydroqhinoline. 
     
     
       12. The method according to claim 6 in which the compound is 1-(0,0-di-isopropyl-thiophosphorylthioacetyl)-trans-decahydroquinoline. 
     
     
       13. A method according to claim 4 in which the compound is of the formula ##SPC11## wherein each of R 1  and R 2  is hydrogen or methyl; R 3  is alkyl of from 1 to 4 carbon atoms, R 4  is alkyl, alkoxy or alkylthio, the alkyl groups having from 1 to 4 carbon atoms; and X is oxygen or sulphur.   
     
     
       14. A method according to claim 13 in which R 2  is hydrogen, R 3  is alkyl of from 1 to 3 carbon atoms and R 4  is alkoxy of from 1 to 3 carbon atoms. 
     
     
       15. The method according to claim 14 in which the compound is 1-(0,0-di-n-propyl-thiophosphorylthio-acetyl)-octahydro-1H-pyrindine. 
     
     
       16. The method according to claim 14 in which the compound is 1-(0,0-dimethyl-thiophosphorylthio-acetyl)-octahydro-1H-pyrindine. 
     
     
       17. The method according to claim 14 in which the compound is 1-(0,0-diethyl-thiophosphorylthio-acetyl)-octahydro-1H-pyrindine. 
     
     
       18. The method according to claim 14 in which the compound is 1-(0,0-diisopropyl-thiophosphorylthio-acetyl)-octahydro-1H-pyrindine. 
     
     
       19. The method according to claim 14 in which the compound is 1-(0,0-dimethyl-phosphorylthio-acetyl)-octahydro-1H-pyrindine. 
     
     
       20. The method according to claim 14 in which the compound is 1-(0,0-di-n-propyl-thiophosphorylthio-acetyl)-4-methyl-octahydro-1H-pyrindine. 
     
     
       21. The method according to claim 13 in which the compound is 1-(0-ethyl-S-n-propyl-phosphorylthio-acetyl)-octahydro-1H-pyrindine.